Pravastatin

Structural formula
Pravastatin sodium salt
General
Non-proprietary name	Pravastatin
other names	3 β -hydroxycompactic acid (β R , δ R , 1 S , 2 S , 6 S , 8 S , 8a R ) -1,2,6,7,8,8a-hexahydro-β, δ, 6-trihydroxy-2-methyl-8 - [(2 S ) -2-methyl-1-oxobutoxy] -1-naphthalenheptanoic acid
Molecular formula	C 23 H 36 O 7
Brief description	colorless solid (sodium salt)
External identifiers / databases
CAS number 81093-37-0 81131-70-6 (sodium salt) PubChem 54687 DrugBank DB00175 Wikidata Q1240093
Drug information
ATC code	C10 AA03
Drug class	Statins
Mechanism of action	competitive HMG-CoA reductase - inhibitor
properties
Molar mass	424.53 g · mol -1
solubility	soluble in methanol and water, slightly soluble in isopropanol, practically insoluble in acetone, acetonitrile, chloroform and ether
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Sodium salt no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	> 12 g kg −1 ( LD 50 ,  rat ,  oral , sodium salt)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pravastatin is a chiral drug from the group of statins , used in the treatment of high cholesterol levels is used. It is taken to prevent cardiovascular complications as long as there is no coronary artery disease.

The natural substance pravastatin is one of the monacolines and is obtained from Nocardia autotrophica (as well as Syncephalastrum nigricans , Absidia coerulea ). Pravastatin was 1991 after lovastatin and simvastatin as a third HMG-CoA reductase - inhibitor ( statin ) in the trade.

Mechanism of action

Pravastatin is a competitive HMG-CoA reductase inhibitor. The HMG-CoA reductase acts as a catalyst in the reduction of 3-hydroxy-3-methylglutaryl-coenzyme A to mevalonate, which is a limiting step in the hepatic cholesterol synthesis. By lowering the cholesterol synthesis, the liver cells increase the number of LDL receptors on the cell surface, so that the LDL uptake into the liver cell increases and thus the LDL level in the blood is reduced.

Side effects

Pravastatin can u. a. Disorders of the gastrointestinal tract (diarrhea, constipation, flatulence), fatigue, muscle pain and headache and joint pain.

Stereoisomerism

Pravastatin contains eight stereogenic centers. So there are theoretically 256 stereoisomers . Only a clearly defined stereoisomer (see formula) in the form of the sodium salt is used as a medicinal substance .

Trade names

Monopreparations

Mevalotin (D, CH), Panchol (A), Pravagamma (D), Pravalip (D), Pravalotin (CH), Pravasin protect (D), Pravasta (CH), Pravastax (CH), Pravatin (CH), Selipran ( CH), Statinoprav (A), numerous generics (D, A, CH)

Individual evidence

1. ↑ Data sheet Pravastatin, Sodium Salt (PDF) from Calbiochem, accessed on December 8, 2015.
2. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1325, ISBN 978-0-911910-00-1 .
3. ↑ Data pravastatin sodium salt hydrate at Sigma-Aldrich accessed on 22 April 2011 ( PDF ).
4. ↑ ^{a b} entry on pravastatin. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
5. ^ Kurt Langbein, Hans-Peter Martin, Hans Weiss: Bitter Pills . 78th edition. Kiepenheuer & Witsch, 2008, ISBN 978-3-462-04004-3 , p. 695.
6. ↑ Red List online, as of September 2009.
7. ↑ AM comp. d. Switzerland, as of September 2009.
8. ↑ AGES-PharmMed, as of September 2009.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !